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0031967318
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Prepared by lithiation (n-BuLi, THF, -78°C, 15 min) of 3-bromofuran, which is expensive but can be prepared; see: G.A. Kraus, and X. Wang Synth. Commun. 28 1998 1093 1096
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85030822184
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note
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3) δ: 200.8 (CO); 199.4 (CHO); 155.9 (C-8); 128.9 (C-7).
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-
-
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30
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85030819396
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note
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This step was carried out as in Scheme 1 (e.g., 8 to 9) but without purification of the intermediates
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32
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0002474209
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For a review on biologically active unsaturated 1,4-dialdehydic terpenoids, see: M. Jonassohn, and O. Sterner Trends Org. Chem. 6 1997 23 43
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F. Compernolle, G. Joly, K. Peeters, S. Toppet, G. Hoornaert, A. Kilonda, and Babady-Bila Tetrahedron 53 1997 12739 12754
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Compernolle, F.1
Joly, G.2
Peeters, K.3
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Hoornaert, G.5
Kilonda, A.6
Babady-Bila7
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35
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85030823207
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note
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This configuration was assigned after observation of a NOE effect between H-11 and H-14
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36
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0000234498
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IBX/AcOEt was used under the conditions described by: J.D. More, and N.S. Finney Org. Lett. 4 2002 3001 3003 6-keto by-products are obtained but the overall yield of the reaction scheme is fair enough to avoid a protection/deprotection sequence of the secondary hydroxyl group (OH-6)
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More, J.D.1
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37
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0344680113
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3) δ: 198.3 (C-16); 193.3 (C-15); 160.4 (C-12); 133.8 (C-13); 76.0 (C-8); 66.4 (C-6); 62.2 (C-9, C-5); 42.5 (C-7); 40.8 (C-3); 39.4 (C-1); 39.0 (C-10); 35.8 (C-14); 32.3 (C-18); 29.6 (C-4); 25.9 (C-11); 22.4, 21.9 (C-19, C-17); 18.0 (C-2); 16.3 (C-20). For data on aframodial: see: S.F. Kimbu, T.K. Njimi, L. Sondengam, J.A. Akinniyi, and J.D. Connoly J. Chem. Soc., Perkin Trans. 1 1979 1303 1305
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Akinniyi, J.A.4
Connoly, J.D.5
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